Punicalin

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Punicalin
Punicalin.png
Names
Other names
4,6-(S,S)-Gallagyl-D-glucose
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C34H22O22/c35-6-1-4-9(19(39)17(6)37)11-15-13-14-16(33(50)56-28(13)23(43)21(11)41)12(22(42)24(44)29(14)55-32(15)49)10-5(2-7(36)18(38)20(10)40)31(48)54-27-8(3-52-30(4)47)53-34(51)26(46)25(27)45/h1-2,8,25-27,34-46,51H,3H2/t8-,25-,26-,27-,34?/m1/s1
    Key: IQHIEHIKNWLKFB-OBOTWMKHSA-N
  • InChI=1/C34H22O22/c35-6-1-4-9(19(39)17(6)37)11-15-13-14-16(33(50)56-28(13)23(43)21(11)41)12(22(42)24(44)29(14)55-32(15)49)10-5(2-7(36)18(38)20(10)40)31(48)54-27-8(3-52-30(4)47)53-34(51)26(46)25(27)45/h1-2,8,25-27,34-46,51H,3H2/t8-,25-,26-,27-,34?/m1/s1
    Key: IQHIEHIKNWLKFB-OBOTWMKHBV
  • c1c2c(c(c(c1O)O)O)-c3c4c5c6c(c(c(c(c6oc4=O)O)O)-c7c(cc(c(c7O)O)O)C(=O)O[C@@H]8[C@@H](COC2=O)OC([C@@H]([C@H]8O)O)O)c(=O)oc5c(c3O)O
Properties
C34H22O22
Molar mass 782.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Punicalin is an ellagitannin. It can be found in Punica granatum (pomegranate) [1] or in the leaves of Terminalia catappa , a plant used to treat dermatitis and hepatitis. [2] [3] It is also reported in Combretum glutinosum , all three species being Myrtales, the two last being Combretaceae.

It is a highly active carbonic anhydrase inhibitor. [4]

Chemistry

The molecule contains a gallagic acid component linked to a glucose.

Related Research Articles

<span class="mw-page-title-main">Pomegranate</span> Fruit-bearing deciduous shrub

The pomegranate is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punicoideae, that grows between 5 and 10 m tall.

<span class="mw-page-title-main">Punicalagin</span> Chemical compound

Punicalagin (Pyuni-cala-jen) is an ellagitannin, a type of phenolic compound. It is found as alpha and beta isomers in pomegranates, Terminalia catappa, Terminalia myriocarpa, and in Combretum molle, the velvet bushwillow, a plant species found in South Africa. These three genera are all Myrtales and the last two are both Combretaceae.

<span class="mw-page-title-main">Carbonic anhydrase inhibitor</span> Class of pharmaceuticals

Carbonic anhydrase inhibitors are a class of pharmaceuticals that suppress the activity of carbonic anhydrase. Their clinical use has been established as anti-glaucoma agents, diuretics, antiepileptics, in the management of mountain sickness, gastric and duodenal ulcers, idiopathic intracranial hypertension, neurological disorders, or osteoporosis.

<span class="mw-page-title-main">Punicic acid</span> Chemical compound

Punicic acid is a polyunsaturated fatty acid, 18:3 cis-9, trans-11, cis-13. It is named for the pomegranate,, and is obtained from pomegranate seed oil. It has also been found in the seed oils of snake gourd.

<span class="mw-page-title-main">CA1 (gene)</span> Protein-coding gene in the species Homo sapiens

Carbonic anhydrase 1 is an enzyme that in humans is encoded by the CA1 gene.

1-<i>alpha</i>-<i>O</i>-Galloylpunicalagin Chemical compound

1-α-O-Galloylpunicalagin is an ester of gallic acid and punicalagin, a type of ellagitannin. It is found in the pomegranate and in Combretum glutinosum.

The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.

<span class="mw-page-title-main">Corilagin</span> Chemical compound

Corilagin is an ellagitannin. Corilagin was first isolated in 1951 from Dividivi extract and from Caesalpinia coriaria, hence the name of the molecule. It can also be found in Alchornea glandulosa and in the leaves of Punica granatum (pomegranate).

<span class="mw-page-title-main">1,2,3,4,6-Pentagalloyl glucose</span> Chemical compound

1,2,3,4,6-Pentagalloylglucose is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.

<span class="mw-page-title-main">Punigluconin</span> Chemical compound

Punigluconin is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate) and in Emblica officinalis. It is a molecule having a hexahydroxydiphenic acid group and two gallic acids attached to a gluconic acid core.

<span class="mw-page-title-main">Punicacortein A</span> Chemical compound

Punicacortein A is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate) and in Osbeckia chinensis.

<span class="mw-page-title-main">Punicacortein D</span> Chemical compound

Punicacortein D is an ellagitannin, a type of phenolic compound. It is found in the bark and heartwood of Punica granatum (pomegranate). The molecule contains a gallagic acid component.

<span class="mw-page-title-main">Punicacortein B</span> Chemical compound

Punicacortein B is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate).

<span class="mw-page-title-main">Punicafolin</span> Chemical compound

Punicafolin is an ellagitannin from the leaves of Punica granatum (pomegranate) and in Phyllanthus emblica.

<span class="mw-page-title-main">Granatin A</span> Chemical compound

Granatin A is an ellagitannin found in the pericarp of Punica granatum (pomegranate). It is a weak carbonic anhydrase inhibitor.

<span class="mw-page-title-main">Granatin B</span> Chemical compound

Granatin B is an ellagitannin found in the fruit of Punica granatum (pomegranate). It is a molecule having an enantiomeric dehydrohexahydroxydiphenoyl group.

<span class="mw-page-title-main">Pomegranate ellagitannin</span> Ellagitannins found in the pomegranate fruit

The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the sarcotestas, rind (peel), bark or heartwood of pomegranates.

<i>Combretum molle</i> Species of tree

Combretum molle, the velvet bushwillow, is a medium to large tree species in the genus Combretum found in western, eastern and southern Africa.

<span class="mw-page-title-main">Casuarinin</span> Chemical compound

Casuarinin is an ellagitannin. It is found in the pericarp of pomegranates. It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana.

<span class="mw-page-title-main">Pedunculagin</span> Chemical compound

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

References

  1. Zhang, Y.; Wang, D.; Lee, R. P.; Henning, S. M.; Heber, D. (2009). "Absence of Pomegranate Ellagitannins in the Majority of Commercial Pomegranate Extracts: Implications for Standardization and Quality Control". Journal of Agricultural and Food Chemistry. 57 (16): 7395–7400. doi:10.1021/jf9010017. PMID   20349921.
  2. Lin, C. C.; Hsu, Y. F.; Lin, T. C.; Hsu, F. L.; Hsu, H. Y. (1998). "Antioxidant and hepatoprotective activity of punicalagin and punicalin on carbon tetrachloride-induced liver damage in rats". The Journal of Pharmacy and Pharmacology. 50 (7): 789–794. doi: 10.1111/j.2042-7158.1998.tb07141.x . PMID   9720629. S2CID   8639399.
  3. Lin, Chun-Ching; Hsu, YF; Lin, TC (1999). "Effects of punicalagin and punicalin on carrageenan-induced inflammation in rats". The American Journal of Chinese Medicine. 27 (3 & 4): 371–376. doi:10.1142/S0192415X99000422. PMID   10592846.
  4. Satomi, H.; Umemura, K.; Ueno, A.; Hatano, T.; Okuda, T.; Noro, T. (1993). "Carbonic anhydrase inhibitors from the pericarps of Punica granatum L". Biological & Pharmaceutical Bulletin. 16 (8): 787–790. doi: 10.1248/bpb.16.787 . PMID   8220326.